Microwave-assisted synthesis of novel 1,2,3-triazole derivatives and their antimicrobial activity

被引:52
作者
Ashok, D. [1 ]
Gandhi, D. Mohan [1 ]
Srinivas, G. [1 ]
Kumar, A. Vikas [1 ]
机构
[1] Osmania Univ, Dept Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
Microwave irradiation; Click chemistry; 1,2,3-Triazoles; Antimicrobial activity; ANTIHYPERTENSIVE ACTIVITY; OXYGENATED CHALCONES;
D O I
10.1007/s00044-013-0880-1
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
An environmentally benign and economic synthesis of 1-[7-(1-benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-dimethyl-chroman-6-yl]-3-aryl-2-propen-1-ones and 1-[5-(1-benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-dimethyl-chroman-6-yl]-3-aryl-propen-1-ones is described. The procedure takes place by the 1,3-dipolar cycloaddition (''click-reaction'') between azides and alkynes catalysed by copper (I) salts. The simplicity of this reaction and the ease of formation and purification of the resulting products have opened new opportunities in generating vast arrays of compounds with biological potential. The structures of the synthesized compounds have been established on the basis of physical and spectral data. All the synthesized compounds were tested in vitro for their antibacterial and antifungal activities. Compounds 8a (R-1=H, R-2=H, R-3=H), 8b (R-1=H, R-2=CH3, R-3=H), 8d (R-1=OCH3, R-2=OCH3, R-3=H), 8e (R-1=OCH3, R-2=OCH3, R-3=OCH3), 13a (R-1=H, R-2=H, R-3=H), 13d (R-1=OCH3, R-2=OCH3, R-3=H) and 13e (R-1=OCH3, R-2=OCH3, R-3=OCH3) showed significant antimicrobial properties.
引用
收藏
页码:3005 / 3018
页数:14
相关论文
共 19 条
[1]   1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY [J].
ALVAREZ, R ;
VELAZQUEZ, S ;
SANFELIX, A ;
AQUARO, S ;
DECLERCQ, E ;
PERNO, CF ;
KARLSSON, A ;
BALZARINI, J ;
CAMARASA, MJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) :4185-4194
[2]   ANTICANCER AND ANTIOXIDANT ACTIVITY OF SYNTHETIC CHALCONES AND RELATED-COMPOUNDS [J].
ANTO, RJ ;
SUKUMARAN, K ;
KUTTAN, G ;
RAO, MNA ;
SUBBARAJU, V ;
KUTTAN, R .
CANCER LETTERS, 1995, 97 (01) :33-37
[3]   Solvent-free microwave-assisted synthesis of E-(1)-(6-benzoyl-3,5-dimethylfuro[3′,2′:4,5]benzo[b]furan-2-yl)-3-(aryl)-2-propen-1-ones and their antibacterial activity [J].
Ashok, D. ;
Sudershan, K. ;
Khalilullah, M. .
GREEN CHEMISTRY LETTERS AND REVIEWS, 2012, 5 (02) :121-125
[4]   One-pot synthesis of novel spiro 2,3,7,8-tetrahydro-benzo[1,2-b:5,4-b′]-dipyran-4,6-dione and 2,3,8,9-tetrahydro-benzo[1,2-b:4,3-b′]dipyran-4,10-dione derivatives [J].
Ashok, D. ;
Shravani, D. .
TETRAHEDRON LETTERS, 2008, 49 (50) :7227-7229
[5]   SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF 4-(1,2-DIHYDRO-2-OXO-1-PYRIDYL)-2H-1-BENZOPYRANS AND RELATED-COMPOUNDS, NEW POTASSIUM CHANNEL ACTIVATORS [J].
BERGMANN, R ;
GERICKE, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :492-504
[6]   VARIATION IN THE AROMATIC RING OF CROMAKALIM - ANTIHYPERTENSIVE ACTIVITY OF PYRANOPYRIDINES AND 6-ALKYL-2H-1-BENZOPYRANS [J].
BURRELL, G ;
CASSIDY, F ;
EVANS, JM ;
LIGHTOWLER, D ;
STEMP, G .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (11) :3023-3027
[7]   Synthesis of 4β-triazole-podophyllotoxin derivatives by azide-alkyne cycloaddition and biological evaluation as potential antitumor agents [J].
Chen, Hong ;
Zuo, Song ;
Wang, Xiaochen ;
Tang, Xiaowei ;
Zhao, Ming ;
Lu, Yanling ;
Chen, Liting ;
Liu, Jing ;
Liu, Yongfeng ;
Liu, Dailin ;
Zhang, Shi ;
Li, Tan .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) :4709-4714
[8]   Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity [J].
Demaray, Jeffrey A. ;
Thuener, Jason E. ;
Dawson, Matthew N. ;
Sucheck, Steven J. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (17) :4868-4871
[9]   3-METHYL-2H-1-BENZOPYRAN POTASSIUM CHANNEL ACTIVATORS [J].
GERICKE, R ;
HARTING, J ;
LUES, I ;
SCHITTENHELM, C .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (10) :3074-3085
[10]   Synthesis and anti-inflammatory effect of chalcones [J].
Hsieh, HK ;
Tsao, LT ;
Wang, JP ;
Lin, CN .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 2000, 52 (02) :163-171